DE2160382A1 - Derivate des 8-Amino-theophyllins, Verfahren zu ihrer Herstellung und entsprechende therapeutische Produkte - Google Patents
Derivate des 8-Amino-theophyllins, Verfahren zu ihrer Herstellung und entsprechende therapeutische ProdukteInfo
- Publication number
- DE2160382A1 DE2160382A1 DE19712160382 DE2160382A DE2160382A1 DE 2160382 A1 DE2160382 A1 DE 2160382A1 DE 19712160382 DE19712160382 DE 19712160382 DE 2160382 A DE2160382 A DE 2160382A DE 2160382 A1 DE2160382 A1 DE 2160382A1
- Authority
- DE
- Germany
- Prior art keywords
- theophylline
- group
- formula
- oil
- cii
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 14
- 230000001225 therapeutic effect Effects 0.000 title claims description 8
- ZZESAIGPDOBLKZ-UHFFFAOYSA-N 8-amino-1,3-dimethyl-7h-purine-2,6-dione Chemical class O=C1N(C)C(=O)N(C)C2=C1NC(N)=N2 ZZESAIGPDOBLKZ-UHFFFAOYSA-N 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 23
- 229960000278 theophylline Drugs 0.000 claims description 18
- 150000001412 amines Chemical class 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- YIUIVFFUEVPRIU-UHFFFAOYSA-N 8-chlorotheophylline Chemical compound O=C1N(C)C(=O)N(C)C2=NC(Cl)=N[C]21 YIUIVFFUEVPRIU-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- SKTFQHRVFFOHTQ-UHFFFAOYSA-N 8-bromo-1,3-dimethyl-7h-purine-2,6-dione Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC(Br)=N2 SKTFQHRVFFOHTQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 20
- 230000000694 effects Effects 0.000 description 15
- 239000000812 cholinergic antagonist Substances 0.000 description 10
- 230000002048 spasmolytic effect Effects 0.000 description 10
- 230000000954 anitussive effect Effects 0.000 description 9
- 241000700159 Rattus Species 0.000 description 8
- 230000003110 anti-inflammatory effect Effects 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 6
- 241000699666 Mus <mouse, genus> Species 0.000 description 6
- 230000000202 analgesic effect Effects 0.000 description 6
- 229940124584 antitussives Drugs 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 description 6
- 230000001882 diuretic effect Effects 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 238000002211 ultraviolet spectrum Methods 0.000 description 6
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 5
- 239000002934 diuretic Substances 0.000 description 5
- 210000001198 duodenum Anatomy 0.000 description 5
- 238000010254 subcutaneous injection Methods 0.000 description 5
- 239000007929 subcutaneous injection Substances 0.000 description 5
- 241000700199 Cavia porcellus Species 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 210000003437 trachea Anatomy 0.000 description 4
- 210000000626 ureter Anatomy 0.000 description 4
- 229930008281 A03AD01 - Papaverine Natural products 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 241000700198 Cavia Species 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 3
- 229910001626 barium chloride Inorganic materials 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 210000002216 heart Anatomy 0.000 description 3
- 229960001340 histamine Drugs 0.000 description 3
- 229960001789 papaverine Drugs 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- -1 2-ethoxy - Chemical class 0.000 description 2
- 208000009079 Bronchial Spasm Diseases 0.000 description 2
- 206010006482 Bronchospasm Diseases 0.000 description 2
- 206010030113 Oedema Diseases 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 229940124630 bronchodilator Drugs 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 229960004126 codeine Drugs 0.000 description 2
- 210000003298 dental enamel Anatomy 0.000 description 2
- 230000000916 dilatatory effect Effects 0.000 description 2
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 230000004936 stimulating effect Effects 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 208000014181 Bronchial disease Diseases 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 102000001554 Hemoglobins Human genes 0.000 description 1
- 108010054147 Hemoglobins Proteins 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 101100496104 Mus musculus Clec2d gene Proteins 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- 101100274534 Rattus norvegicus Clec2d11 gene Proteins 0.000 description 1
- 101100274532 Rattus norvegicus Ocil gene Proteins 0.000 description 1
- 241000885184 Scaris Species 0.000 description 1
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
- 102000003929 Transaminases Human genes 0.000 description 1
- 108090000340 Transaminases Proteins 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
- 229960004373 acetylcholine Drugs 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 210000004100 adrenal gland Anatomy 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000001004 anti-acetylcholinic effect Effects 0.000 description 1
- 230000001760 anti-analgesic effect Effects 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000000621 bronchi Anatomy 0.000 description 1
- 230000003182 bronchodilatating effect Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000306 component Substances 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 239000003218 coronary vasodilator agent Substances 0.000 description 1
- 230000003001 depressive effect Effects 0.000 description 1
- 230000010339 dilation Effects 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000002489 hematologic effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N monoethyl amine Natural products CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 229940124641 pain reliever Drugs 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000003033 spasmogenic effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
- C07D473/08—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 1 and 3, e.g. theophylline
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7043890A FR2116301B1 (OSRAM) | 1970-12-07 | 1970-12-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2160382A1 true DE2160382A1 (de) | 1972-06-22 |
Family
ID=9065323
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712160382 Pending DE2160382A1 (de) | 1970-12-07 | 1971-12-06 | Derivate des 8-Amino-theophyllins, Verfahren zu ihrer Herstellung und entsprechende therapeutische Produkte |
Country Status (11)
| Country | Link |
|---|---|
| AU (1) | AU3654871A (OSRAM) |
| BE (1) | BE776278A (OSRAM) |
| CA (1) | CA925088A (OSRAM) |
| CH (1) | CH546772A (OSRAM) |
| DE (1) | DE2160382A1 (OSRAM) |
| ES (1) | ES397562A1 (OSRAM) |
| FR (1) | FR2116301B1 (OSRAM) |
| GB (1) | GB1366319A (OSRAM) |
| LU (1) | LU64394A1 (OSRAM) |
| OA (1) | OA03925A (OSRAM) |
| ZA (1) | ZA718135B (OSRAM) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110174363A (zh) * | 2019-01-09 | 2019-08-27 | 北京九强生物技术股份有限公司 | 6-磷酸葡萄糖脱氢酶突变体及其在制备检测试剂中的用途 |
-
1970
- 1970-12-07 FR FR7043890A patent/FR2116301B1/fr not_active Expired
-
1971
- 1971-11-29 OA OA54423A patent/OA03925A/xx unknown
- 1971-11-29 CH CH1736671A patent/CH546772A/fr not_active IP Right Cessation
- 1971-12-01 ES ES397562A patent/ES397562A1/es not_active Expired
- 1971-12-02 LU LU64394D patent/LU64394A1/xx unknown
- 1971-12-03 GB GB5621371A patent/GB1366319A/en not_active Expired
- 1971-12-06 DE DE19712160382 patent/DE2160382A1/de active Pending
- 1971-12-06 ZA ZA718135A patent/ZA718135B/xx unknown
- 1971-12-06 BE BE776278A patent/BE776278A/xx unknown
- 1971-12-06 AU AU36548/71A patent/AU3654871A/en not_active Expired
- 1971-12-07 CA CA129547A patent/CA925088A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2116301B1 (OSRAM) | 1974-08-30 |
| CA925088A (en) | 1973-04-24 |
| CH546772A (fr) | 1974-03-15 |
| OA03925A (fr) | 1975-08-14 |
| LU64394A1 (OSRAM) | 1972-06-19 |
| ES397562A1 (es) | 1974-06-16 |
| GB1366319A (en) | 1974-09-11 |
| BE776278A (fr) | 1972-04-04 |
| FR2116301A1 (OSRAM) | 1972-07-13 |
| AU3654871A (en) | 1973-06-14 |
| ZA718135B (en) | 1972-08-30 |
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